I’m not a narcissist, nor am I a sociopath.

As such, I have insecurities.

Most of these insecurities stem from childhood.

And like most ‘bad’ things, in small doses, they can be good for us.

Insecurities can fuel our fire. They can drive us to seek out external validation and as a result, achieve more and become more than we wouldhave without them.

There’s little doubt that many great innovations of the last few centuries were a result of innovators looking to prove themselves.

On the flipside, peaking early can be inherently bad for us, and keep us from self-actualization. (Read: When You Peak Early, You Lose)

In my case, insecurity, societal influences, a desire to keep up with the Joneses (whoever they are), and a belief that more money and status would make me happy pushed me forward.

It drove me to secure my Master’s degree in a year while working 25 hours a week. It enabled me to hustle my way into gigs at global powerhouses like EY, KPMG, and Macquarie Bank, despite having gone to public schools in Melbourne’s working-class western suburbs and having attended run of the mill colleges.

After several years in the corporate space, my hunger hadn’t faded, and I pursued entrepreneurship. This culminated in my founding several companies, one of which — unlike the others — Collective Campus, went on to become one of Australia’s fastest-growing companies.

By ordinary measures of success, I guess you could say I was successful.

But… I wasn’t happy.

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Searching for Truth

Legend has it that one day Socrates and his student Plato were walking down the beach in deep conversation. Plato asked Socrates to tell him the truth. Long story short, Socrates dunked Plato’s head into the water, only to resurface it once Plato was about to blackout (some say Socrates had to revive him). When Plato asked Socrates why he did that, Socrates responded with “when you desire the truth like you desired air right now, then you shall have it”.

And I guess that’s what I was looking for. The truth.

We seek answers to big questions when we go through difficulty. In my case, I had worked hard for almost a decade to become somebody, yet the supposed void and irritability I was confronted with forced me to seek out philosophy.

Listening to an episode of the Tim Ferriss show, I stumbled upon Stoicism, and by extension, other schools and works of philosophy.

Before these ideas could save me, they had to destroy me.

These are the ideas that stole my ambition.

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The Man Who Craves More is Poor

It is not the man who has too little, but the man who craves more, that is poor.What does it matter how much a man has laid up in his safe, or in his warehouse, how large are his flocks and how fat his dividends, if he covets his neighbor’s property, and reckons, not his past gains, but his hopes of gains to come? Do you ask what is the proper limit to wealth? It is, first, to have what is necessary, and, second, to have what is enough. — Seneca

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Wealth Required by Vanity is Infinite

The wealth required by nature is limited and is easy to procure; but the wealth required by vain ideals extends to infinity. — Epicurus

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Living a False Purpose

Too many people go through life with a false purpose, driven either by money, social status, ego, a sense of self-worth and so on. What they do usually doesn’t align with their natural inclinations or strengths so they ultimately wind up miserable and unfulfilled. — Robert Greene

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Conquering the Need to Conquer the World

Philosopher to Alexander the Great

This man has conquered the world! What have you done?” The philosopher replied without an instant’s hesitation, “I have conquered the need to conquer the world.” — Philosopher to Alexander the Great (after being told to show respect to the conquerer after having asked him to stop blocking his sun)

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Desire is a Sin

There is no greater sin than desire, no greater curse than discontent. He who knows that enough is enough will always have enough — Lao Tzu

Or this gem…

Life is too important to be taken seriously. — Oscar Wylde

And the knockout blow…

Consider past times, thou shalt see the same things: some marrying, some bringing up children, some sick, some dying, some fighting, some feasting, some flattering, some boasting, some suspecting, some undermining, some wishing to die, some fretting, some wooing, some hoarding, some seeking after magistracies, and some after kingdoms. And is not that their age quite over, and ended? Again, consider now the times of Trajan. There likewise thou seest the very self-same things, and that age also is now over and ended. — Marcus Aurelius

Aurelius himself quotes a famous passage in Homer’s Iliad which echoes this sentiment. In it, the lives of mortals are compared to leaves that grow in the spring, flourish for a season and then fall and die, only to be replaced by others.

Translation: Chill the f*ck out.

You could say that I became a lot more mellow.

True to Lao Tzu’s and Seneca’s sentiments, I realized that I had enough. More things wouldn’t make me happier. Realizing this, I found a form of contentment. This had me questioning my entire approach to work and life.

Having had my world view shift from #hustle to #ctfo, my alarm clock was set to 6 am instead of 5 am, and my workdays went from 10 hours to my trumpeting 6 hour days in Harvard Business Review (something I am still a huge advocate of).

A note on monocausality: It is lazy for one to suggest that a single X caused Y. In truth, almost all Ys are the result of a coalescence of Xs. My mellowing out was no doubt influenced by these philosophical ideas that I bought into, but also my getting older (I’m 35 now), biology, the arrival fallacy (I’ve made it…what now?), potential dissatisfaction with other aspects of life, and myriad other factors.

But then, just like that, philosophy kindly returned my drive and ambition, with one key difference.

Finding the Truth?

Legendary physicist Richard Feynman said, “we can never be sure we’re right, we can only be sure we’re wrong”. As such, I don’t think that the following ideas represent the absolute truth. But they do make sense.

The following ideas funneled my ambition away from false purposes and into meaningful pursuits, aligned with my values.

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The Virtuous Life

Only through living virtuously can we achieve human flourishing. — Aristotle

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Values Alignment

Happiness is the achievement of your values. — Ayn Rand

Reflecting on my values, I sought freedom from things and freedom to do things, meaningful work, time with people I care about.

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Purpose

Making an encore appearance, the following excerpts from Marcus Aurelius’ Meditations…

Nothing should be done without purpose.

At dawn, when you have trouble getting out of bed, tell yourself: “I have to go to work — as a human being. What do I have to complain of, if I’m going to do what I was born for — the things I was brought into the world to do? Or is this what I was created for? To huddle under the blankets and stay warm?

So you were born to feel “nice”? Instead of doing things and experiencing them? Don’t you see the plants, the birds, the ants and spiders and bees going about their individual tasks, putting the world in order, as best they can? And you’re not willing to do your job as a human being? Why aren’t you running to do what your nature demands?

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Happiness is a Pointless Goal

‘Happiness’ is a pointless goal. Don’t compare yourself with other people, compare yourself with who you were yesterday. No one gets away with anything, ever, so take responsibility for your own life.

It’s all very well to think the meaning of life is happiness, but what happens when you’re unhappy? Happiness is a great side effect. When it comes, accept it gratefully. But it’s fleeting and unpredictable. It’s not something to aim at — because it’s not an aim. And if happiness is the purpose of life, what happens when you’re unhappy? Then you’re a failure. And perhaps a suicidal failure.Happiness is like cotton candy. It’s just not going to do the job. — Jordan Peterson

These ideas gave me a sense of clarity, and helped me focus my energy and ambition on what truly matters.

Not seeking our riches to satisfy public opinion (the fallacy being that the more you have the more people tend to resent you anyway).

It meant:

• less comparing myself
• less making decisions to appease other people or opinion
• less buying ‘the things’ for validation
• more contentment with ‘enough’
• doing work that matters instead of just seeking out money (interestingly, doing work that matters ends up making you money)

As Seneca put it, if you live according to opinion you will never be rich, but if you live according to nature, you will never be poor.

Now, it’s not about just building a business that makes money. It’s about building businesses the create impact. It’s about sharing whatever wisdom I have attained with people who have the potential to create impact themselves.

Whether it be my writing for Harvard Business Review, my last book Employee to Entrepreneur, hosting my podcast Future Squared, or taking my children’s entrepreneurship program, Lemonade Stand, to the world, itis all about empowering other people to be their best, but to do so in a way that is geared towards some greater purpose than simply collecting gold coins.

It also means I spend more time with family, more time with friends, and more time outside of the office walls in nature, learning how to surf, hiking new spots, and…enjoying life.

Like Naval Ravikant puts it, if you play stupid games you win stupid prizes.Competition can blind us to what really matters, and when you take the time to reflect on what you value, as opposed to what society supposedly values, living in accordance with that changes your whole life’s outlook.

Yes, philosophy stole my ambition…to make lots of money, compare myself to no end and never be content, no matter how much I achieved. But it redirected that ambition into doing meaningful work, enjoying life’s pleasures and living a life true to myself.

Like a philosopher is thought to have said before me, I have conquered the need to conquer the world.